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Holiday rentals in Cheshire

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Top-rated holiday rentals in Cheshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

Wintergreen Gardens, at the William Becroft House
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bathroom
Wintergreen Gardens, at the William Becroft HouseOur 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, king bedroom, en-suite bath, kitchenette w/refrige, micro, coffee maker and TV. Sunroom opens onto private patios for sunning, morning coffee or a nook to read a book. Walk downtown for outdoor dining or a drink. 5 min. drive to two vineyards. Guidebook for food/entertainment ideas. **No cooking devices allowed. No pet=no pets. Laundry for extended stay guests.
Spacious in-law apartment steps from Choate
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Spacious in-law apartment steps from ChoatePrivate apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio
A secluded cosy place
Entire residential home · 8 guests · 4 beds · 2 bathrooms
A secluded cosy placeA secluded cosy place - 4 bedroom single family house on a 2 acre lot. Very close to Sleeping Giant State Park and Quinnipiac University.

Holiday rentals for every style

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Popular amenities for Cheshire holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cheshire

  1. Farm stay
  2. Bethany
The Little House on Locket's Meadow
₹8,252 per night
SUPERHOST
  1. Private room
  2. Hamden
Freshly Renovated Private Suite by the trail!
₹5,028 per night
SUPERHOST
  1. Entire rental unit
  2. Southington
#1 - STAY WITH A SUPERHOST - BEAUTIFUL 3 BR APT!
₹12,700 per night
  1. Entire rental unit
  2. Wallingford
Wallingford Getaway
₹9,377 per night
  1. Private room
  2. Wallingford
Cuarto amueblado
₹2,626 per night
SUPERHOST
  1. Entire rental unit
  2. Southington
#5- *A MUST SEE* 3 BR APT IN A GREAT LOCATION!
₹15,893 per night
SUPERHOST
  1. Private room
  2. Hamden
Cozy Private Bedroom right by the trail!
₹3,666 per night
  1. Entire residential home
  2. Hamden
Sleeping Giant Getaway on MT. Carmel
₹43,135 per night
SUPERHOST
  1. Entire residential home
  2. Southington
#9 - *STUNNING*RENOVATED* *4BR HOUSE*
₹13,803 per night
  1. Entire rental unit
  2. Cheshire
Deer Run Apartment
₹7,127 per night
SUPERHOST
  1. Entire residential home
  2. Cheshire
Pool House
₹9,752 per night
  1. Private room
  2. Southington
Large Private Room & Location w/ AMAZING LOUNGE #2
₹2,626 per night